EP1919616A2 - Process for preparing alkoxylation catalyst and alkoxylation process - Google Patents
Process for preparing alkoxylation catalyst and alkoxylation processInfo
- Publication number
- EP1919616A2 EP1919616A2 EP06789743A EP06789743A EP1919616A2 EP 1919616 A2 EP1919616 A2 EP 1919616A2 EP 06789743 A EP06789743 A EP 06789743A EP 06789743 A EP06789743 A EP 06789743A EP 1919616 A2 EP1919616 A2 EP 1919616A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- catalyst
- compound
- ethoxylated alcohol
- alkaline earth
- earth metal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0211—Oxygen-containing compounds with a metal-oxygen link
- B01J31/0212—Alkoxylates
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/068—Polyalkylene glycols
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
- B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/23—Calcium
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/20—Complexes comprising metals of Group II (IIA or IIB) as the central metal
- B01J2531/24—Strontium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0201—Oxygen-containing compounds
- B01J31/0204—Ethers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
Definitions
- the present invention relates to the preparation of an alkoxylation catalyst and to a process of alkoxylation using the thus prepared catalyst.
- Alkoxylated esters and compounds containing active hydrogen atoms such as alcohols find utility in a wide variety of products, e.g., surfactants.
- an alkoxylation reaction involving a compound having an active hydrogen is conducted by the condensation of an alkylene oxide using a suitable catalyst. Because of the nature of the reaction, a mixture of product species is obtained having a rather wide range of molecular weights.
- an aikoxylation catalyst of improved activity is produced. Additionally, catalysts prepared according to a preferred embodiment of the present invention exhibit greater stability vis-a-vis settling of slurried catalyst particles. Further, aikoxylation catalysts according to preferred embodiments of the present invention, block unwanted growth of ethyoxlated alcohols in the catalyst which results in reduced formation of high molecular weight ethylene oxide adducts in the resulting products produced using the catalysts, and thereby reduces visual haze.
- an aikoxylation catalyst is prepared by reacting a catalyst precursor comprising an ethoxylated alcohol and a dispersed alkaline earth metal compound, with propylene oxide under conditions to propoxylate at least a portion of the ethoxylated alcohol.
- a catalyst precursor comprising an ethoxylated alcohol and a dispersed alkaline earth metal compound
- propylene oxide under conditions to propoxylate at least a portion of the ethoxylated alcohol.
- the catalysts of the present invention are based on the unexpected finding that by subjecting certain prior art alkoxylation catalysts to propoxylation conditions, surprising results with respect to catalyst activity and stability as well as an improvement in the appearance of products produced using the catalyst, are achieved.
- the prior art catalysts which are treated according to the process of the present invention to produce the alkoxylation catalysts of the present invention are referred to herein as "catalyst precursors.”
- Catalyst A One of the catalyst precursors, referred to herein as Catalyst A, is disclosed in U.S. Patents 4,775,653 ('653 Patent) and 5,220,077 ('077 Patent). As disclosed in the '653 and '077 Patents, Catalyst A is prepared by admixing and reacting an ethoxylated alcohol mixture containing an ethoxylated alcohol having the general formula:
- R 1 -O-(C 2 H 4 O) P H I wherein R 1 is an organic radical containing from about 1 to about 30 carbon atoms and p is an integer of from 1-30, an alkaline earth metal-containing compound which is at least partially dispersible in the ethoxylated alcohol mixture, an inorganic acid, and a metal alkoxide selected from compounds having the formulas
- R 2 , R3, R4, and R5 are each a hydrocarbon radical containing from about 1 to about 30, preferably from about 8 to about 14, carbon atoms.
- the ethoxylated alcohols used can be prepared by methods well known in the art for preparing ethylene oxide adducts of alcohols.
- the ethoxylated alcohol mixture used in preparing Catalyst A typically contains free alcohol, the amount and type of which will vary depending upon the source of the ethoxylated alcohol. Generally speaking, the ethoxylated alcohol mixture will contain from about 1 % to about 60% by weight free alcohol.
- the alkaline earth metal compound used is one which is at least partially dispersible in the ethoxylated alcohol.
- the term "dispersible” refers to a compound which solublizes or otherwise interacts with the ethoxylated alcohol in such a manner that it becomes a new species of alkaline earth metal compound. It is to be understood, however, that inasmuch as the mechanism is not completely understood, the term “dispersible” or “soluble” is not intended to be limited to the formation of a truly dissolved alkaline earth metal species as would be commonly understood in the case of ordinary solublization . While compounds such as calcium and strontium hydride, calcium and strontium acetate, calcium and strontium oxalate, etc. may be used, it is preferred that the alkaline earth metal compound be calcium or strontium oxide, calcium or strontium hydroxide, calcium or strontium hydride or a mixture thereof.
- the inorganic acids useful include the acids themselves as well as “acid salts".
- inorganic acids include sulphuric acid, hydrochloric acid, hydrofluoric acid, phosphoric acid, pyrophosphoric acid, ammonium biflouride, ammonium sulfate, etc.
- oxy acids such as sulphuric acid.
- the mol ratio of the alkaline earth metal compound to the metal alkoxide can vary from about 1 :1 to about 10:1 , based on alkaline earth metal compound and metal of the alkoxide, respectively.
- the mol ratio of the inorganic acid to the metal alkoxide can vary from about 0.25:1 to about 4:1 , based on the ratio of the acid equivalent e.g. acid hydrogens, in the inorganic acid to the metal of the alkoxide, respectively.
- the combined concentration of the alkaline earth metal compound, the inorganic acid and the metal alkoxide be present in an amount of from about 1 to about 10% by weight, the ethoxylated alcohol and diluents such as free alcohol being present in an amount of from about 90-99% by weight.
- free alcohol content can range, from about 1 % by weight to about 60% by weight.
- the order of addition of the various components of Catalyst A is immaterial with the exception that the alkaline earth metal compound must be added prior to addition of the metal alkoxide.
- the process can also be carried out by reversing the order of addition of the metal alkoxide and the inorganic acid.
- Catalyst A can contain, with advantage, organic acids.
- Suitable organic acids are those carboxylic acids which have greater miscibility in hydrocarbon solvents than in water.
- Such carboxylic acids which may generally be considered fatty acids, have a carbon chain length versus acid functionality which provides their greater miscibility or solubility in hydrocarbons.
- Non-limiting examples of fatty acids include those natural or synthetic mono-functional carboxylic acids wherein the carbon chain length is greater than about 5 carbon atoms, generally from about 5 to about 15 carbon atoms.
- Suitable acids include hexanoic, octanoic, nonanoic, 2-ethyl hexanoic, neodecanoic, isooctanoic, stearic, napthanoic, and mixtures or isomers of such acids. While it is preferred that the acids, if used, be saturated, they may optionally contain other functional groups such as hydroxyl groups, amine groups, etc. which do not interfere with the process. It has been found that the use of the fatty acids leads to a better dispersion of the alkaline earth metal compound and that the active catalyst suspension is more stable in terms of the solids remaining dispersed.
- a typical ethoxylated alcohol is admixed with a suitable alkaline earth metal containing compound such as calcium oxide and the mixture stirred for a suitable period of time until at least some of the calcium compound disperses or solublizes in the ethoxylated alcohol.
- a suitable alkaline earth metal containing compound such as calcium oxide
- this is accomplished by stirring, or other means of agitation to achieve intimate and thorough contact, at a temperature of generally from about 25°C to about 150 0 C (usually below the boiling point of the ethoxylated alcohol) for a sufficient period of time.
- the dispersion time can vary from about 0.5 hours to about 20 hours. Longer times can be used if desired.
- the inorganic acid is then slowly or incrementally added.
- the metal e.g., aluminum alkoxide is then added and stirring of the mixture continued and the mixture heated to a temperature and for a sufficient period of time to effect at least a partial exchange reaction between the alkoxide groups of the metal alkoxide and the hydroxyl group of the ethoxylated alcohol.
- Catalyst A The precise temperature to which Catalyst A is heated will, of course, depend upon the nature of the components employed. However, as noted above, the heating is usually carried out at a temperature and for a period of time sufficient to effect at least a partial exchange reaction between the alkoxide groups of the metal alkoxide and the hydroxyl group of the ethoxylated alcohol. This point can generally be determined by the evolution of alcohol which distills out of the mixture. It is preferred that the heating be carried on until the mixture has reached a substantially constant boiling point.
- the desired activation temperature shoul for a given pressure, approximate the boiling point of a substantial fraction of the free alcohols derived from the R 2 , R 3 and R 4 group of the metal alkoxide.
- 300 0 C and more preferably from about 230°-260°C Lower temperatures may be employed when the process is conducted under reduced pressure, e.g. at a pressure of about 150-300 Torr, temperature in the range of about 160 0 C to about 210 0 C are suitable.
- the desired temperature range can be determined by sampling the dispersion as it is being heated at various times during the heating cycle and subjecting the samples to an ethoxylation reaction. When the desired degree of activity is achieved in the ethoxylation reaction, heating can be discontinued. Generally, however, the time of heating can vary from about 0.1 hour to about 5 hours, generally in the range of from about 0.2 hour to about 1 hour.
- Catalyst B is formed by reacting an ethoxylated alcohol mixture, a alkaline earth metal compound that is at least partially dispersible in the ethoxylated alcohol mixture and a carboxylic acid.
- the ethoxylated alcohols useful in forming Catalyst B are the same as those defined by Formula 1.
- the ethoxylated alcohol mixture used can be prepared by methods well known in the art for preparing alkylene oxide adducts of alcohols. Alternately, the alkylene oxide adducts can be prepared according to the process of the present invention.
- the ethoxylated alcohol mixture used in preparing Catalyst B typically contains free alcohol, the amount and type of which will vary depending upon the source of the ethoxylated alcohol. Generally speaking, the ethoxylated alcohol mixture will contain from about 1% to about 60% by weight free alcohol.
- the alkaline earth metal compounds used in preparing Catalyst B are as described above with respect to Catalyst A.
- the carboxylic acids used in preparing Catalyst B are as described above with respect to Catalyst A.
- the inorganic acids that are useful in preparing Catalyst B are those as described above with respect to Catalyst A.
- the relative amounts of the various components can vary widely, and in general, are defined above with respect to Catalyst A.
- Catalyst B the ethoxylated alcohol mixture, the alkaline earth metal compound, the carboxylic acid, and the neutralizing acid are reacted or combined under conditions that prevent any significant loss of water that is either initially present or formed during the reaction.
- Preventing loss of water is typically accomplished by conducting the reaction at a low enough temperature, e.g., room temperature, to prevent loss of water.
- a low enough temperature e.g., room temperature
- super-atmospheric pressure can be used to prevent loss of water.
- the reaction is conducted at elevated temperatures under reflux to prevent loss of water.
- Catalyst B the alkaline earth metal compound, e.g., calcium hydroxide, and the ethoxylated alcohol mixture are charged into a suitable stirred vessel equipped with a reflux condenser, following which the carboxylic acid is added. Generally, the three components are mixed at room temperature, although higher temperatures can be used. This reaction mixture is then heated generally to a temperature of from about 30° to 45°C for a period of time sufficient to solubilize the calcium-containing compound. Generally speaking, the reaction mixture is reacted for a period of from about 0.5 to about 2 hours.
- the alkaline earth metal compound e.g., calcium hydroxide
- the ethoxylated alcohol mixture are charged into a suitable stirred vessel equipped with a reflux condenser, following which the carboxylic acid is added. Generally, the three components are mixed at room temperature, although higher temperatures can be used. This reaction mixture is then heated generally to a temperature of from about 30° to 45°C for a period of time sufficient to solub
- a mineral acid e.g., sulfuric acid
- the reaction mixture can optionally be sparged with an inert gas such as nitrogen.
- a suitable catalyst precursor e.g., Catalyst A or Catalyst B, described above, is reacted with propylene oxide under propoxylation conditions to effect at least propoxylation of at least a portion of the ethoxylated alcohols present in the catalyst precursor.
- the formula of ethoxylated alcohols present in either of the catalyst precursors is given by Formula I above.
- Particularly preferred ethoxylated/propoxylated species coming within Formula IV which are useful in the present invention are those wherein Ri contains from 8 to 14 carbon atoms, p is from 2 to 6 and t is from 1 to 3, most preferably from 1 to 1.5. It will be understood that, as in the case of all alkoxylated species of alcohols, there is a distribution of the alkoxy groups, the numbers above referring to the average number of ethoxy/propoxy groups present in the alkoxylated species.
- the catalysts of the present invention are prepared by reacting one of the catalyst precursors with the desired amount of propylene oxide in a standard alkoxylation reactor.
- the propoxylation reaction is conducted at a temperature from 95 to 200 0 C and from 15 to 75 psig propylene oxide
- catalyst precursors 85 gram portions of catalyst precursors were separately subjected to propylene oxide addition in the standard alkoxylation reactor at a temperature of 120 to 150 0 C and a pressure of 40 to 50 psig propylene oxide (PPO) so as to result in the addition of 1.0 to 1.5 mols of propylene oxide.
- PPO propylene oxide
- the thus prepared catalysts were compared with Catalyst A and Catalyst B, i.e., the catalyst precursor, to determine activity.
- the catalyst samples were tested for activity on the basis of time to effect addition of a given amount of ethylene oxide to an ALFOL® 12 alcohol, a alcohol marketed by Sasol North America, Inc. In all cases, the amount of catalyst employed was 0.1 wt. %.
- Table 1 shows the results using the various catalyst in preparing an ethoxylated Ci 2 alcohol containing 7 mols of ethylene oxide.
- the catalysts according to the present invention contained 1 mol of propylene oxide as indicated by Catalyst A + 1 PPO, Catalyst B + 1 PPO, etc.
- Table 2 shows results for the addition of two mols of ethylene oxide io me Ci 2 alcohol.
- Example 2 This Example demonstrates the effect of adding different levels of propylene oxide to the catalyst precursors in terms of catalyst stability, i.e., the ability of the catalyst to remain as a generally homogeneous' dispersion over a period of time.
- the procedure of Example 1 was followed with respect to the propoxylation of Catalyst B.
- all of the propoxylated samples exhibited greater stability, i.e., remained better dispersed than the non-propoxylated Catalyst B. This dispersion improvement was not noticed with respect to similarly propoxylated samples of
- Example 1 The procedure of Example 1 was followed with respect to determining the effect of propoxylation of the catalyst precursors vis-a-vis ethoxylation activity with the exception that the alcohol employed was SafolTM 23, an essentially linear C12-13 binary alcohol marketed by Sasol North America, Inc. In all cases, 7 mols of ethylene oxide were added to the alcohol.
- Table 3 The results comparing Catalyst B and a catalyst according to the present invention are shown in Table 3 below.
- Example 1 The procedure of Example 1 was followed in terms of preparing 7 mol ethoxylates of the SafolTM 23 alcohol. Both in the case of propoxylated Catalyst A and B 1 it was found that from 1.0' to 1.5 mols of propylene oxide added resulted in less residual catalyst haze. It was also noted with respect to Catalyst A propoxylated at the 0.5 mol level that there appeared to be an increase in haze of the ethoxylated product.
- the process of the present invention provides alkoxylation catalysts that, as compared to prior art alkoxylation catalysts, exhibit greater activity, are more stable, and produce a product with less haze.
- the amount of propylene oxide added to the catalyst precursor is tailored. Modifications of the compositions, procedures and conditions disclosed herein that will still embody the concept of the improvements described should readily suggest themselves to those skilled in the art, and are intended to be encompassed within the spirit of the invention presently disclosed herein as well as the scope of the appended claims.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US11/217,779 US20070060770A1 (en) | 2005-09-01 | 2005-09-01 | Process for preparing alkoxylation catalyst and alkoxylation process |
PCT/US2006/031625 WO2007030277A2 (en) | 2005-09-01 | 2006-08-11 | Process for preparing alkoxylation catalyst and alkoxylation process |
Publications (2)
Publication Number | Publication Date |
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EP1919616A2 true EP1919616A2 (en) | 2008-05-14 |
EP1919616A4 EP1919616A4 (en) | 2010-11-03 |
Family
ID=37836331
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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EP06789743A Withdrawn EP1919616A4 (en) | 2005-09-01 | 2006-08-11 | Process for preparing alkoxylation catalyst and alkoxylation process |
Country Status (8)
Country | Link |
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US (2) | US20070060770A1 (en) |
EP (1) | EP1919616A4 (en) |
JP (1) | JP5089590B2 (en) |
KR (1) | KR101383660B1 (en) |
CN (1) | CN101287552B (en) |
CA (1) | CA2620838C (en) |
MX (1) | MX313589B (en) |
WO (1) | WO2007030277A2 (en) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070213554A1 (en) * | 2005-09-01 | 2007-09-13 | Matheson Kenneth L | Process for preparing alkoxylation catalyst and alkoxylation process |
US20080167501A1 (en) | 2007-01-08 | 2008-07-10 | Bayer Materialscience Llc. | High productivity alkoxylation processes |
US9266821B2 (en) * | 2009-10-16 | 2016-02-23 | Harcros Chemicals Inc. | Process for making fatty amides |
CA2861224A1 (en) | 2012-01-30 | 2013-08-08 | Dow Global Technologies Llc | Process for preparing high molecular weight polymers by polymerizing epoxide monomers |
AU2013338136B2 (en) | 2012-10-29 | 2017-07-13 | Sasol Performance Chemicals Gmbh | Activators for the viscosification of non-aqueous fluids |
CN103041860B (en) * | 2013-01-24 | 2015-03-25 | 凤台精兴生物科技有限公司 | Alkali compound catalyst used in synthesis reaction of nonyl phenol polyoxyethylene ether |
JP6637039B2 (en) * | 2014-06-17 | 2020-01-29 | サソール(ユーエスエイ)コーポレーシヨン | Catalyst composition, method for producing the same, and method for alkoxylating alcohol using such a catalyst |
CN109317187B (en) * | 2018-11-19 | 2021-08-03 | 江苏钟山化工有限公司 | Catalyst for synthesis of fatty acid ester alkoxylates and application thereof |
AR118833A1 (en) | 2019-05-03 | 2021-11-03 | Sasol Performance Chemicals Gmbh | NON-AQUEOUS DEFOAMING COMPOSITIONS AND THEIR USE IN FOAM CONTROL OF NON-AQUEOUS FOAMS |
US20230117983A1 (en) | 2020-04-02 | 2023-04-20 | Sasol (Usa) Corporation | Water-Soluble Coloring Compositions Comprising Alcohol Alkoxylates with 40 to 160 Ethoxy Units Derived from Primary Alcohols Having a Chain Length Between 20 and 30 Carbon Atoms |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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US4483941A (en) * | 1982-09-02 | 1984-11-20 | Conoco Inc. | Catalysts for alkoxylation reactions |
AU570489B2 (en) * | 1983-07-05 | 1988-03-17 | Union Carbide Corporation | Alkoxylation using calcium catalysts |
US4835321A (en) * | 1987-04-28 | 1989-05-30 | Vista Chemical Company | Alkoxylaton process using calcium based catalysts |
US4775653A (en) * | 1987-04-28 | 1988-10-04 | Vista Chemical Company | Alkoxylation process using calcium based catalysts |
JP2890322B2 (en) * | 1990-02-01 | 1999-05-10 | ユニオン、カーバイド、ケミカルズ、アンド、プラスチックス、カンパニー、インコーポレイテッド | Alkoxylation method using modified III-B metal-containing bimetal or polymetal catalyst |
US5386045A (en) * | 1991-08-22 | 1995-01-31 | Vista Chemical Company | Process for alkoxylation of esters and products produced therefrom |
US5220077A (en) * | 1992-08-19 | 1993-06-15 | Vista Chemical Company | Alkoxylation process |
US5627121A (en) * | 1995-06-15 | 1997-05-06 | Condea Vista Company | Process for preparing alkoxylation catalysts and alkoxylation process |
US6147246A (en) * | 1999-12-23 | 2000-11-14 | Condea Vista Company | Process for preparing alkoxylated dialkyl carbonate compounds |
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2005
- 2005-09-01 US US11/217,779 patent/US20070060770A1/en not_active Abandoned
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2006
- 2006-08-11 EP EP06789743A patent/EP1919616A4/en not_active Withdrawn
- 2006-08-11 CA CA2620838A patent/CA2620838C/en active Active
- 2006-08-11 WO PCT/US2006/031625 patent/WO2007030277A2/en active Application Filing
- 2006-08-11 KR KR1020087006072A patent/KR101383660B1/en active IP Right Grant
- 2006-08-11 CN CN2006800383483A patent/CN101287552B/en active Active
- 2006-08-11 JP JP2008529087A patent/JP5089590B2/en active Active
-
2008
- 2008-02-28 MX MX2008002915A patent/MX313589B/en active IP Right Grant
-
2011
- 2011-12-05 US US13/311,273 patent/US8329609B2/en active Active
Non-Patent Citations (2)
Title |
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No further relevant documents disclosed * |
See also references of WO2007030277A2 * |
Also Published As
Publication number | Publication date |
---|---|
KR20080042890A (en) | 2008-05-15 |
WO2007030277A3 (en) | 2007-12-27 |
CA2620838C (en) | 2013-05-07 |
US20120078001A1 (en) | 2012-03-29 |
CN101287552A (en) | 2008-10-15 |
JP5089590B2 (en) | 2012-12-05 |
WO2007030277A2 (en) | 2007-03-15 |
MX313589B (en) | 2013-09-24 |
MX2008002915A (en) | 2008-05-02 |
JP2009506885A (en) | 2009-02-19 |
CN101287552B (en) | 2012-07-18 |
KR101383660B1 (en) | 2014-04-09 |
US8329609B2 (en) | 2012-12-11 |
EP1919616A4 (en) | 2010-11-03 |
US20070060770A1 (en) | 2007-03-15 |
CA2620838A1 (en) | 2007-03-15 |
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